Ethylene dione
Encyclopedia
Ethylene dione or ethylenedione, also called dicarbon dioxide, ethenedione, or ethene 1,2-dione, is the name given to a hypothetical chemical compound
with the formula
C2O2 or O=C=C=O. It would be an oxide
of carbon
(an oxocarbon
), specifically a dimer of carbon monoxide
(CO). It can be thought of as ketene
of glyoxylic acid
(OHCCOOH).
Early theoretical studies suggested that the triplet state
of C2O2 might be stable, although it would be much less so than its relatives CO2
and C3O2
. However, many synthesis attempts have failed to turn up any trace of it. Recent research indicates that the molecule
may be extremely short lived, decomposing into two molecules of carbon monoxide
in less than 10−8 seconds.
On the other hand, the divalent
anion C2O22−, called acetylenediolate
, is reasonably stable in the absence of water.
claimed that he had synthesized this compound, which he called glyoxylide, and that it was an antidote
to the "toxins" that caused a long list of ailments, including diabetes and cancer
. Neither claim was ever confirmed, and the drug was classified as a fraud by the FDA.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
C2O2 or O=C=C=O. It would be an oxide
Oxide
An oxide is a chemical compound that contains at least one oxygen atom in its chemical formula. Metal oxides typically contain an anion of oxygen in the oxidation state of −2....
of carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
(an oxocarbon
Oxocarbon
An oxocarbon or oxide of carbon is an inorganic compound consisting only of carbon and oxygen.The simplest and most common oxocarbons are carbon monoxide and carbon dioxide...
), specifically a dimer of carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
(CO). It can be thought of as ketene
Ketene
A ketene is an organic compound of the form R'RC=C=O. The term is also used specifically to mean ethenone, the simplest ketene, where R' and R are hydrogen atoms.Ketenes were first studied as a class by Hermann Staudinger.-Formation:...
of glyoxylic acid
Glyoxylic acid
Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially....
(OHCCOOH).
Early theoretical studies suggested that the triplet state
Triplet state
A spin triplet is a set of three quantum states of a system, each with total spin S = 1 . The system could consist of a single elementary massive spin 1 particle such as a W or Z boson, or be some multiparticle state with total spin angular momentum of one.In physics, spin is the angular momentum...
of C2O2 might be stable, although it would be much less so than its relatives CO2
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...
and C3O2
Carbon suboxide
Carbon suboxide, or tricarbon dioxide, is an oxide of carbon with chemical formula C3O2 or O=C=C=C=O. Its four cumulative double bonds make it a cumulene...
. However, many synthesis attempts have failed to turn up any trace of it. Recent research indicates that the molecule
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...
may be extremely short lived, decomposing into two molecules of carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
in less than 10−8 seconds.
On the other hand, the divalent
Valence (chemistry)
In chemistry, valence, also known as valency or valence number, is a measure of the number of bonds formed by an atom of a given element. "Valence" can be defined as the number of valence bonds...
anion C2O22−, called acetylenediolate
Acetylenediol
Acetylenediol, or ethynediol, is a chemical substance with formula HO-C≡C-OH. It is the diol of acetylene. Acetylenediol is unstable in the condensed phase, although its tautomer glyoxal H2H is well known.-Detection:...
, is reasonably stable in the absence of water.
Koch's glyoxylide
In the 1940s, Detroit physician W. F. KochWilliam Frederick Koch
William Frederick Koch was a U. S. medical doctor and pharmaceutical entrepreneur. In the 1940s he marketed glyoxylide, a drug which he claimed would cure cancer. The claims were never scientifically proved, and he was considered a charlatan by the FDA.-Biography:William Koch got a BA in...
claimed that he had synthesized this compound, which he called glyoxylide, and that it was an antidote
Antidote
An antidote is a substance which can counteract a form of poisoning. The term ultimately derives from the Greek αντιδιδοναι antididonai, "given against"....
to the "toxins" that caused a long list of ailments, including diabetes and cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
. Neither claim was ever confirmed, and the drug was classified as a fraud by the FDA.
See also
- CyclohexanehexoneCyclohexanehexoneCyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is a organic compound with formula C6O6, the sixfold ketone of cyclohexane...
C6O6, also called triquinoyl, formally a trimer of ethylene dione.